Journal ArticleDOI
Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog
Thomas F. Spande,H. M. Garraffo,M. W. Edwards,Herman J. C. Yeh,Lewis K. Pannell,John W. Daly +5 more
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TLDR
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane represents a unique new class of alkaloids.Abstract:
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane. It represents a unique new class of alkaloidsread more
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Journal ArticleDOI
Nicotine is out: nicotinic agonists may have utility as analgesics.
Pamela Flood,M. Imad Damaj +1 more
TL;DR: Perioperative nicotine administration was associated with a statistically significant reduction in cumulative opioid consumption and a statistically insignificant reduction in pain scores 24 hours after surgery, both of which were small.
Book ChapterDOI
Fármacos analgésicos en desarrollo
TL;DR: In this article, el capitulo resume la situacion de la investigacion de nuevos farmacos en desarrollo for tratar el dolor, and describe the obstaculos que debe superar un nuevo farmaco antes de poder ser introducido como terapia.
Patent
Epibatidine and derivatives thereof as nicotine cholinergic receptor agonists
TL;DR: In this paper, the authors present methods of treatment utilizing pharmaceutical compositions comprising an effective nicotine agonist amount of epibatidine (1) or a synthetic 7-azabicyclo[2.1]-heptane or heptene derivative thereof, and a pharmaceutically acceptable earner, excipient or diluent.
Journal ArticleDOI
Synthesis of α-chloropyridine-containing oximes of 3β,5-dihydroxy-6-ketosteroids
TL;DR: New derivatives of 6-ketoximes containing α-chloropyridine neonicotinoid groups characteristic of bioactive compounds were synthesized by formation of oximes of cholestane and stigmastane 3β,5-dihydroxy-6-ketosteroids with O-(2-chlorOPyridin-5-ylmethyl)hydroxylamine in the presence of zinc or tin(IV) chloride as mentioned in this paper.
Journal ArticleDOI
N-Arylmethyl-7-azabicyclo[2.2.1]heptane derivatives: synthesis and reaction mechanisms
TL;DR: In this paper, a mechanistic investigation using DFT has been carried out to explain the results observed in this work, and it has been shown that the bromination of the key intermediates is stereoselective leading to major trans-3-cis-4-dibromides (14, 17, and 20), whose mild base-mediated heterocyclization (on compound 14), or the two-step acid hydrolysis plus base-promoted cyclization, on compounds 17 and 20, gave products 6 and 7 in good yield.